Water-insoluble coloring matter compound, ink using the water-insoluble coloring matter compound, thermal transfer recording sheet and resist composition for color filter
a technology of water-soluble coloring matter and ink, which is applied in the direction of thermal imaging, instruments, optical elements, etc., can solve the problems of reducing the contrast ratio of color display in the liquid crystal display, limiting the lightness of the color filter, and providing high transmittance of backlight, etc., to achieve high lightness and chroma, high solubility of solvents, and magenta chromaticity
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production example 1
Production Example of Compound (1)
[0131]10.4 g (80 mmol) of ethyl acetoacetate and 0.7 g (6.4 mmol) of sodium carbonate were suspended in 40 ml, of 1,2-dichlorobenzene of 14.3 g (40 mmol) of 4-bromo-1-butylaminoanthraquinone, and the suspension was stirred at 175° C. for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and diluted with 50 mL of 2-propylalcohol and 50 ml of hexane. The solid was filtered, and washed with 100 mL of 2-propylalcohol to obtain 8 g of an intermediate product (1) corresponding to Compound C. 3.6 mL of 2-ethylhexylamine, 292 mg of copper(I) iodide, and 4.7 g of sodium carbonate were added to a solution of 75 mL of dimethylformamide of 7 g (14.6 mmol) of the intermediate product (1), and the reaction was conducted at 100° C. for 2 hours. After the reaction was completed, the reaction solution was cooled, diluted with 200 mL of ethyl acetate, and filtered. Column, chromatography refining (toluene / THF) was perfo...
production example 2
Production Example of Compound (4)
[0137]The same operation as that in Production Example 1 was performed except that ethyl acetoacetate in Production Example 1 was replaced by ethyl benzoylacetate. Thus, 6.6 g (yield of 32%) of a compound (4) was obtained.
[0138]The solubility in water of the compound at room temperature and that at 60° C. were measured, and it was found that both were less than 1% in terms of mass percentage.
[0139]
[0140][1]1H NMR (400 MHz, CDCl3, Room temperature): δ [ppm]=0.96 (dt, 9H, J=25.0, 7.21 Hz), 1.36-1.39 (m, 4H), 1.45-1.61 (m, 6H), 1.79 (t, 3H, J=6.18 Hz), 3.37-3.41 (m, 2H), 4.39 (s, 2H), 7.32-7.47 (m, 4H), 4.75 (tt, 2 Hz, J=7.56, 2.44 Hz), 7.72 (d, 1H, J=10.1 Hz), 7.97-8.03 (m, 3H), 8.55 (dd, 1H, J=7.79, 1.37 Hz), 10.9 (s, 1H)
[0141][2] Mass spectrometry (ESI-TOF): m / z=535.3001 (M+H)+
[0142][3] UV / Vis spectral analysis: λmax=558 nm
production example 3
Production Example of Compound (5)
[0143]The same operation as that in Production Example 1 was performed except that ethyl acetoacetate in Production Example 1 was replaced by ethyl 4-methoxybenzoylacetate. Thus, 5.4 g (yield of 24%) of a compound (6) was obtained.
[0144]The solubility in water of the compound at room temperature and that at 60° C. were measured, and it was found that both were less than 1% in terms of mass percentage.
[0145]
[0146][1]1H NMR (400 MHz, CDCl3, Room temperature): δ [ppm]=0.90 (dt, 9H, J=24.9, 7.21 Hz), 1.31 (t, 4H, J=3.66 Hz), 1.44 (dd, 4H, J=14.9, 7.56 Hz), 1.52 (dd, 2H, J=16.5, 7.33 Hz), 1.73 (t, 3H, J=6.18 Hz), 3.78 (s, 1H), 4.33 (d, 2H, 43.1 Hz), 6.86 (d, 2H, J=9.16 Hz), 7.24 (t, 1H, J=11.5 Hz), 7.34 (t, 1H, J=7.79 Hz), 7.51 (t, 1H, J=7.56 Hz), 7.65 (d, 1H, J=9.62 Hz), 7.92 (d, 2H, J=8.70 Hz), 8.01 (d, 1H, J=8.24 Hz), 10.8 (s, 1H)
[0147][2] Mass spectrometry (ESI-TOF): m / z=565.3048 (M+H)+
[0148][3] UV / Vis spectral analysis: λmax=557 nm
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